Cottage holiday rentals in Chincoteague

A cozy cottage exterior is presented with a light blue façade and a welcoming front porch. The entrance features a small overhang and steps leading to the front door, accompanied by neatly trimmed bushes and a well-maintained lawn under clear blue skies.

4.94 out of 5 average rating, 199 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.

4.96 out of 5 average rating, 162 reviews

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

4.98 out of 5 average rating, 148 reviews

A charming cottage stands surrounded by lush grass, with a large tree providing shade in the foreground. The white exterior features a welcoming entrance with step access, flanked by neatly trimmed bushes and colorful potted plants. A serene open field extends beyond the cottage.

Cottage in Greenbush

Bell Farm Cottage Comfy, cozy, peaceful, quiet

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

4.99 out of 5 average rating, 255 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Three shorter stays available: July 19-21, October 23-26 and November 11-14. Message me so I can send special invite. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

4.85 out of 5 average rating, 115 reviews

Ivy's Cottage - Lovely Downtown Cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

4.95 out of 5 average rating, 152 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.

4.95 out of 5 average rating, 183 reviews

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

4.91 out of 5 average rating, 116 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

Privacy, peace, relaxation, togetherness … this cottage is the perfect place for memory-making with your family and friends! The kitchen is stocked with every spice and tool you may require to create a delicious meal, which can be enjoyed at the breakfast bar, large dining table, or outside, surrounded by the tranquil Virginia ambience. The shed, equipped with kayaks, paddle board, crabbing gear, bicycles, beach stuff chairs, has all you may need for a day on the bay or at the ocean.

An outdoor seating area is showcased with a cozy sectional sofa covered in gray fabric. Colorful tropical-patterned pillows are arranged on the sofa, complementing a rectangular coffee table placed on a patterned outdoor rug featuring leaf designs. Sunlight creates a bright atmosphere.

4.88 out of 5 average rating, 197 reviews

Sunshine Retreat-Large Deck-Enclosed cozy porch!

SUMMER Dates still available: July 14-16. 2 nights July 19-23 Aug 9-14 Aug 21-27 Two bedroom cottage on the famous island of Chincoteague! Walking distance to restaurants, shops, farmers market on Church Street / School Street and LIVE music downtown waterfront park! Two enclosed porches to have morning coffee & large deck for chillin sunbathing or reading a good book. Enclosed outdoor shower - HOT and COLD water. NON-SMOKING (please smoke outside near parking area if necessary)

The exterior of a charming cottage is depicted, featuring a white wooden facade and a metal roof. A small stone patio with a bistro table and chairs sits at the entrance, surrounded by lush greenery and flowering plants. Two windows invite natural light into the space.

4.96 out of 5 average rating, 123 reviews

Little Cottage on the Creek

Experience Onancock....."a little slice of nowhere else". Whether you are looking for a romantic getaway for two, or just some rest and relaxation off the beaten path, Little Cottage on the Creek is the perfect place for your stay. Beautifully furnished and freshly renovated, this cozy waterfront cottage has all the comforts of home. Enjoy magnificent views of Onancock Creek along with the serenity for which the Eastern Shore is famous.

Superhost

A charming two-story house is situated in a grassy area, featuring red shutters and a sign reading 'Island Breeze Vacation Rental' in front. Flower beds with vibrant blooms surround the sign. A porch with steps leads to the entrance of the home.

Cottage in Saxis

4.85 out of 5 average rating, 142 reviews

ISLAND BREEZE Near Chincoteague Island

Waterman’s fishing village Surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. Walking distance to beach (located on Dennis Lane) Kayaking & Canoeing Wildlife Fishing Pier Boat Ramp Marina Public Pavilion Ice Cream Shop 1-Restaurant (Capt E’s Hurricane Grill & Tiki Bar) Museum Multiple Seafood Shanty’s (Steamed Crabs Available during season)

4.88 out of 5 average rating, 252 reviews

A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.

Cottage in Reedville

Private point on the Bay🌤hammock, hot tub, kayaks❤️

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

Popular amenities for cottage rentals in Chincoteague

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The front exterior of the creek house is shown, featuring a welcoming porch with steps leading up. A colorful flag waves gently, and vibrant greenery surrounds the area, while a white railing offers a pleasant border. The house has a light beige facade complemented by green accents.

Cottage in Newark

4.89 out of 5 average rating, 54 reviews

Cropper Creek House

Cottage in Marion Station

An aerial view showcases a rustic-modern house surrounded by greenery. Red pathways lead to the entrance, and a wooden deck is visible with steps leading up to the front door. In the background, a private pool and shaded seating areas offer outdoor relaxation options.

4.78 out of 5 average rating, 49 reviews

Year Round Playground - Rare Rustic-Modern Getaway

4.88 out of 5 average rating, 60 reviews

The cottage exterior features a welcoming design with a red front door, surrounded by a gravel pathway and lush greenery. Large windows brighten the facade, while a porch with railings offers a relaxing space to enjoy nature.

Cottage in Selbyville

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV

4.89 out of 5 average rating, 253 reviews

A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.

Cottage in Reedville

Bay cottage 🏖on the beach. Stunning views🏝

4.97 out of 5 average rating, 74 reviews

The exterior of a blue cottage is shown, featuring a sloped roof and a welcoming front porch with seating. Lush green grass surrounds the home, and a large area of trees is visible in the background, providing a natural setting.

Cottage in Snow Hill

Hot Tub Haven 2 Mi to Beach! ‘Christy's Cottage’

Pet-friendly cottage rentals

Aerial view of a peaceful coastal retreat set on a spacious property surrounded by lush greenery and water. A sandy beach extends along the shoreline, complemented by tranquil marshlands and distant woodlands. The house is positioned towards the center, offering a sense of privacy amidst nature.

4.87 out of 5 average rating, 62 reviews

Peaceful 5 bedroom cottage on the Eastern Shore...

A welcoming entrance is framed by neatly trimmed hedges and a well-maintained grassy area. The front porch features decorative railings and steps leading up to a door with a wreath. An American flag is displayed, adding to the home's charm.

4.79 out of 5 average rating, 24 reviews

ESVA Down by the Sea & Pet Friendly

Superhost

Two wooden Adirondack chairs are positioned on a weathered dock, facing towards a calm waterway. A shaded structure is visible on the left, while boats are anchored in the distance against a backdrop of blue skies dotted with white clouds.

4.73 out of 5 average rating, 110 reviews

SNUG HARBOR waterfront cottage with a grand view!

4.95 out of 5 average rating, 40 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

4.89 out of 5 average rating, 27 reviews

A beach area features a colorful striped umbrella providing shade over two blue folding chairs positioned on the sandy shore. Lush grass and a calm body of water create a serene environment, with wooden posts partially visible in the background.

Cottage in Diggs

Chesapeake Bay Beach Front cabin

4.91 out of 5 average rating, 58 reviews

A waterfront view features a peaceful beach with soft sand, bordered by rocky shorelines. The cottage's sunroom is visible, along with surrounding trees and other houses, creating a tranquil setting. Calm waters reflect the sky, enhancing the serene atmosphere.

Cottage in Reedville

Waterfront Cottage with Private Chesapeake Beach

4.84 out of 5 average rating, 32 reviews

A light-filled living area showcases a navy sofa facing a mounted television. A striped ottoman sits on a woven rug, while a plant adds a touch of greenery. Dining chairs and natural light from surrounding windows create an inviting space for relaxation.

Cottage in Ocean City

Bungalow 611 | Quick to Assateague & OC

4.95 out of 5 average rating, 64 reviews

Cottage in Exmore

Waterfront Sunsets | Pet-Friendly Escape | No Fees

Private cottage rentals

4.9 out of 5 average rating, 197 reviews

A single-story home sits nestled among lush greenery, featuring a welcoming front porch with a wooden railing. A set of steps leads up to the entrance, flanked by large windows adorned with green shutters, complementing the home's neutral exterior.

Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

The exterior of a charming white cottage is showcased, featuring two sets of stairs leading to the front porch. The well-maintained lawn is punctuated by a small garden area, and a decorative figure can be seen near the entrance.

4.98 out of 5 average rating, 54 reviews

Waterfowl Watch Chincoteague & bikes August dates

The front exterior of the Victorian farmhouse features a light blue facade with white trim. A covered porch provides access to the entrance, surrounded by greenery and lawn. The house is three stories tall, displaying multiple windows that allow natural light.

5 out of 5 average rating, 70 reviews

Waterfront Victorian home in downtown Onancock

5 out of 5 average rating, 61 reviews

Cottage in Smith Island

IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental

Cottage in Deal Island Historic District

The waterfront cottage is viewed at dusk, featuring a spacious deck with a dining area and seating. Illuminated windows suggest a cozy interior. The private pier extends toward the water, lined with post lights, and natural landscaping complements the setting.

4.96 out of 5 average rating, 23 reviews

"Cozy" Waterfront Cottage with Private Pier

4.92 out of 5 average rating, 66 reviews

Holiday Cottages -"Sea Star"~POOL~3 mi. to Beach

4.96 out of 5 average rating, 76 reviews

A charming cottage exterior is showcased, featuring a wooden deck surrounded by white railings. Steps lead up to the entrance, bordered by smooth landscaping and ornamental grasses. Shadows from nearby trees create a serene ambiance against a cloudy sky.

Cottage in Selbyville

Country Cottage -7 Miles from Fenwick Island Beach

The exterior of Westview Cottage is shown, featuring a well-maintained lawn with lush greenery. Floor-to-ceiling glass doors are visible, reflecting the surrounding landscape and allowing natural light into the cottage. Trees and shrubs frame the view, enhancing the serene atmosphere.